17550-38-8

Upstream product

• 108-24-7 acetic anhydride 
• 55304-68-2 Benzoic acid (1S,2S)-2-acetoxy-3-hydroxy-7-oxa-bicyclo[4.1.0]hept-4-en-1-ylmethyl ester 
• 98-88-4 benzoyl chloride 
• 55304-71-7 C₂₂H₂₂O₅ 
• 55304-65-9 Benzoic acid (1S,2R)-2-acetoxy-5-oxo-7-oxa-bicyclo[4.1.0]hept-3-en-1-ylmethyl ester 
• 74766-85-1 trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]-cyclohexa-4,6-diene 
• 532-32-1 sodium benzoate 
• 74766-79-3 DL-1,2-di-O-acetyl-(1,3/2)-3-benzoyloxymethyl-5-cyclohexene-1,2-diol 
• 74766-77-1 DL-di-O-acetyl-(1,3/2,4,6)-3,4-dibromo-6-benzoyloxymethyl-1,2-cyclohexanediol 
• 69982-70-3 3,4-di-O-acetyl-2,6-dibromo-2,6-dideoxy-5a-carba-β-DL-glucopyranosyl bromide 
• 74766-83-9 DL-1,2-di-O-acetyl-(1,4/2,3)-3,4-dibromo-6-bromomethyl-5-cyclohexene-1,2-diol 
• 74766-84-0 DL-1,2-di-O-acetyl-(1,6/2,5)-3-benzoyloxymethyl-5,6-dibromo-3-cyclohexene-1,2-diol 
• 74766-78-2 3,4-di-O-acetyl-1,5-anhydro-6-bromo-2,6-dideoxy-5a-carba-DL-arabino-hex-1-enitol 
• 55304-67-1 Benzoic acid (1R,2S)-2-acetoxy-6-oxo-4,8-dioxa-tricyclo[5.1.0.0^3,5]oct-1-ylmethyl ester 

Downstream Products

• 99773-35-0 DL-1,2,3-tri-O-acetyl-(1,2/3)-1-C-acetoxymethyl-4-cyclohexene-1,2,3-triol 
• 20421-13-0 DL-5,6-di-O-acetyl-1,2:3,4-dianhydro-(1,2,6/3,4,5)-1-C-benzoyloxymethyl-1,2,3,4,5,6-cyclohexanehexol 

Relevant academic research and scientific papers

Enantiospecific syntheses of (+)-crotepoxide, (+)-boesenoxide, (+)-β- senepoxide, (+)-pipoxide acetate, (-)-iso-crotepoxide, (-)-senepoxide, and (- )-tingtanoxide from (-)-quinic acid

A convenient strategy that is ideally suited for the Construction of all the naturally occurring cyclohexane diepoxides and cyclohexene epoxides is described. The key intermediate 12, a 1,3-cyclohexadiene, has been prepared from (-)-quinic acid in 11 steps with 18% overall yield: Singlet oxygen photooxygenation of the 1,3-cyclohexadiene followed by rearrangement of the resultant endoperoxides with either cobalt-meso-tetraphenylporphyrin or trimethyl phosphite afforded enantiopure (+)-crotepoxide, (+)-boesenoxide, and (-)-iso-crotepoxide or (-)-senepoxide, (+)-β-senepoxide, (+)-pipoxide acetate, and (-)-tingtanoxide, respectively.

Conversion of β-Senepoxide to Crotepoxide: Total Synthesis of (+)-Crotepoxide

Total synthesis of (+)-crotepoxide has been accomplished by chemical conversion of (+)-β-senepoxide which was prepared from (-)-7-endo-oxabicyclohept-5-ene-2-carboxylic acid.

SYNTHESIS AND EPOXIDATION OF TRANS-5,6-DIACETOXY-1-BENZOYLOXYMETHYL-1,3-CYCLOHEXADIENE.

The title substituted 1,3-cyclohexadiene was prepared in three steps from the readily available DL-1,2-di-O-acetyl-(1,3/2)-3-bromomethyl-5-cyclohexene-1,2-diol. Epoxidation of it with m-chloroperoxybenzoic acid in 1,2-dichloroethane afforded several stere

SYNTHESIS AND EPOXIDATION OF TRANS-5,6-DIACETOXY-1-BENZOYLOXYMETHYL-1,3-CYCLOHEXADIENE

Epoxidation of a newly prepared trans-5,6-diacetoxy-1-benzoyloxymethyl-1,3-cyclohexadiene by m-chloroperbenzoic acid in dichloroethane gave several isomeric compounds of the biologically important highly oxygenated cyclohexane derivatives.

STEREOSELECTIVE SYNTHESIS OF (+/-)-SENEPOXYDE AND (+/-)-CROTEPOXIDE

Stereoselective synthesis of (+/-)-senepoxyde and (+/-)-crotepoxyde is described starting from 2-hydroxymethyl-1,4-benzoquinone through the retro-Diels-Alder reaction.